The preparation of 25-hydroxycholesterol from cholesterol and sitosterol will be completed. The critical step is the selective remote hydroxylation. This has been accomplished in the following form. Cholesterol was nitrated and reduced to 6 beta-acetamidocholestanol. Remote oxidation and elimination of acetamide were conducted as a single step to produce chol-5-ene-3 beta, 24-diol in an overall yield of 14% from cholesterol. Sitosterol was converted to norchol-5-ene-3 beta, 23-diol similarly. Both diols should be convertible to 25-hydroxycholesterol in two steps by conventional procedures. It is also proposed to exploit a new discovery. Cholestenone can be directly oxidized to 25-hydoxychol-5-en-30-one (approximately 35% yield by gc) and sitostenone is oxidized directly to 23-hydroxynorchol-5-en-3-one. These reactions have the potential for producing progesterone, testosterone, and their derivatives from cholesterol and sitosterol in efficient and economical processes.